4-Bromophenol → 4-(4-Bromophenoxy)tetrahydro-2H-pyran

HRID 636935Notes

Reaction equation

HRID 636935 reaction equation
C(OC(N=NC(OCC)=O)=O)C.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.O[CH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 78084-BromophenolHCID 11776TriphenylphosphineHCID 74956Tetrahydro-4H-pyran-4-olHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 162161274-(4-Bromophenoxy)tetrahydro-2H-pyran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 4.0 mL of diethyl-azodicarboxylate in 20 mL of dry tetrahydrofuran was added at 5° C. to a stirred solution of 3.5 g of 4-bromo-phenol, 2.4 mL of 4-hydroxy-tetrahydropyran and 6.6 g triphenylphosphine in 75 mL of tetrahydrofuran within 30 minutes. Stirring was continued at room temperature for 72 hours. The solvent was evaporated in vacuo and the residue chromatographed on silica gel (ethyl acetate) yielding 5.6 g of 4-(4-bromo-phenoxy)-tetrahydropyran as a white solid. M.p. 53-55° C., EI-MS: 256 (M+).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue chromatographed on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-250716f224574d1e8ec5c7fd0f1b3404
Source dataset
uspto-grants-2001_02
Patent number
US06194409B1

Reaction notes

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